(E)-(S)-5-Hydroxy-3,6-dimethyl-hept-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(S)-5-Hydroxy-3,6-dimethyl-hept-2-enoic acid ethyl ester
CAS No.:916912-61-3
Molecular Formula:C₁₁H₂₀O₃
Molecular Weight:200.278
Hs Code.:

Synonyms:(E)-(S)-5-Hydroxy-3,6-dimethyl-hept-2-enoic acid ethyl ester

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Chemical Property of (E)-(S)-5-Hydroxy-3,6-dimethyl-hept-2-enoic acid ethyl ester

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Technology Process of (E)-(S)-5-Hydroxy-3,6-dimethyl-hept-2-enoic acid ethyl ester

There total 1 articles about (E)-(S)-5-Hydroxy-3,6-dimethyl-hept-2-enoic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 38836-21-4,65651-63-0
(S)-4-hydroxy-5-methylhexan-2-one

: 916912-61-3
(E)-(S)-5-Hydroxy-3,6-dimethyl-hept-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 42.55 g / imidazole / dimethylformamide / 24 h

2.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C

2.2: hexane; tetrahydrofuran / 1 h / -78 °C

3.1: 13.85 g / aq. HF / acetonitrile / 20 °C

With 1H-imidazole; hydrogen fluoride; lithium diisopropyl amide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetonitrile; 2.2: Peterson reaction;
DOI:10.1002/chem.200600599

Reference yield:

: 916912-61-3
(E)-(S)-5-Hydroxy-3,6-dimethyl-hept-2-enoic acid ethyl ester

: pyrrolidine-2-carboxylic acid 6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-oxazol-2-yl)-5-hydroxy-1-isopropyl-3-methyl-heptyl ester

Guidance literature:: Multi-step reaction with 17 steps

1.1: H₂ / Pd/C / methanol / 12 h / 20 °C / 760 Torr

2.1: 3.69 g / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

3.1: pyridine / CH₂Cl₂ / 0 °C

4.1: aq. K₂CO₃ / methanol / 5 h

5.1: Dess-Martin reagent / CH₂Cl₂ / 3 h / 0 °C

6.1: CF₃SO₃H; Et₃B; DIPEA / hexane; CH₂Cl₂ / 0.5 h / -10 °C

6.2: 91 percent / TiCl₄ / hexane; CH₂Cl₂ / 2 h

7.1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

8.1: PPTs / 24 h

9.1: 82 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene

10.1: TsOH / methanol

11.1: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h

12.1: NaClO₂; NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 1 h

13.1: HATU; DIPEA / CH₂Cl₂ / 24 h

14.1: 86 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 3 h / -78 °C

15.1: N-methylaniline / [Pd(PPh₃)4] / tetrahydrofuran / 2 h

16.1: HATU; DIPEA / CH₂Cl₂ / 48 h / 20 °C

17.1: tetrabutylammonium fluoride / tetrahydrofuran

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; triethyl borane; trifluorormethanesulfonic acid; diethylamino-sulfur trifluoride; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-methylaniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; sodium hypochlorite; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 5.1: Dess-Martin oxidation;
DOI:10.1002/chem.200600599

Reference yield:

: 916912-61-3
(E)-(S)-5-Hydroxy-3,6-dimethyl-hept-2-enoic acid ethyl ester

: 916913-02-5
C₆₄H₉₁N₅O₁₂Si

Guidance literature:: Multi-step reaction with 16 steps

1.1: H₂ / Pd/C / methanol / 12 h / 20 °C / 760 Torr

2.1: 3.69 g / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

3.1: pyridine / CH₂Cl₂ / 0 °C

4.1: aq. K₂CO₃ / methanol / 5 h

5.1: Dess-Martin reagent / CH₂Cl₂ / 3 h / 0 °C

6.1: CF₃SO₃H; Et₃B; DIPEA / hexane; CH₂Cl₂ / 0.5 h / -10 °C

6.2: 91 percent / TiCl₄ / hexane; CH₂Cl₂ / 2 h

7.1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

8.1: PPTs / 24 h

9.1: 82 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene

10.1: TsOH / methanol

11.1: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO₃ / NaClO / CH₂Cl₂; H₂O / 1 h

12.1: NaClO₂; NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 1 h

13.1: HATU; DIPEA / CH₂Cl₂ / 24 h

14.1: 86 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / 3 h / -78 °C

15.1: N-methylaniline / [Pd(PPh₃)4] / tetrahydrofuran / 2 h

16.1: HATU; DIPEA / CH₂Cl₂ / 48 h / 20 °C

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; triethyl borane; trifluorormethanesulfonic acid; diethylamino-sulfur trifluoride; 2,4,6-trichlorobenzoyl chloride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-methylaniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; sodium hypochlorite; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 5.1: Dess-Martin oxidation;
DOI:10.1002/chem.200600599